# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Waro Nakanishi' _publ_contact_author_email NAKANISI@SYS.WAKAYAMA-U.AC.JP _publ_section_title ; Extended Hypervalent E'---E-E---E' 4c-6e (E, E' = Se, S) Interactions: Structure, Stability, and Reactivity of 1-(8-PhE'C10H6)EE(C10H6E'Ph-8')-1' ; loop_ _publ_author_name 'Waro Nakanishi' 'Satoko Hayashi' 'Sayuri Morinaka' 'Norihiro Tokitoh' # Attachment 'B805678A_1CIF.doc' data_1 _database_code_depnum_ccdc_archive 'CCDC 626066' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1 Se2S2' _chemical_melting_point ? _chemical_formula_moiety 'C32 H22 S2 Se2' _chemical_formula_sum 'C32 H22 S2 Se2' _chemical_formula_weight 628.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall ' -P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.579(3) _cell_length_b 11.979(4) _cell_length_c 12.141(4) _cell_angle_alpha 91.773(4) _cell_angle_beta 102.912(4) _cell_angle_gamma 110.758(2) _cell_volume 1260.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.0 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 3.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3341 _exptl_absorpt_correction_T_max 0.5093 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8096 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4329 _reflns_number_gt 3971 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crystal Clear' _computing_cell_refinement 'Crystal Clear' _computing_data_reduction ? _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4329 _refine_ls_number_parameters 413 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0223 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_ref 0.0532 _refine_ls_wR_factor_gt 0.0526 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.40643(2) 0.169539(17) 0.189671(15) 0.01034(7) Uani 1 1 d . . . Se2 Se 0.23137(2) 0.099405(16) 0.009498(15) 0.01012(7) Uani 1 1 d . . . S1 S 0.61818(5) 0.30021(5) 0.41538(4) 0.01202(11) Uani 1 1 d . . . S2 S 0.01466(5) 0.00973(4) -0.21680(4) 0.01176(11) Uani 1 1 d . . . C1 C 0.6078(2) 0.21216(17) 0.15379(16) 0.0110(4) Uani 1 1 d . . . C2 C 0.6095(2) 0.18604(18) 0.04316(17) 0.0145(4) Uani 1 1 d . . . H1 H 0.520(3) 0.157(2) -0.0142(18) 0.027(6) Uiso 1 1 d . . . C3 C 0.7462(2) 0.19731(19) 0.01195(18) 0.0159(4) Uani 1 1 d . . . H2 H 0.743(2) 0.1793(18) -0.0647(18) 0.013(5) Uiso 1 1 d . . . C4 C 0.8823(2) 0.23378(18) 0.09289(17) 0.0135(4) Uani 1 1 d . . . H3 H 0.973(3) 0.239(2) 0.0780(18) 0.022(6) Uiso 1 1 d . . . C5 C 1.0318(2) 0.30189(18) 0.28939(17) 0.0141(4) Uani 1 1 d . . . H4 H 1.113(3) 0.3019(18) 0.2638(16) 0.015(5) Uiso 1 1 d . . . C6 C 1.0453(2) 0.33407(19) 0.40078(18) 0.0167(4) Uani 1 1 d . . . H5 H 1.142(3) 0.3548(19) 0.4575(17) 0.014(5) Uiso 1 1 d . . . C7 C 0.9133(2) 0.33267(18) 0.43436(17) 0.0147(4) Uani 1 1 d . . . H6 H 0.922(2) 0.3583(19) 0.5145(19) 0.022(6) Uiso 1 1 d . . . C8 C 0.7713(2) 0.29660(17) 0.35791(16) 0.0113(4) Uani 1 1 d . . . C9 C 0.7505(2) 0.25828(16) 0.24048(16) 0.0097(4) Uani 1 1 d . . . C10 C 0.8884(2) 0.26550(17) 0.20722(16) 0.0113(4) Uani 1 1 d . . . C11 C 0.5809(2) 0.42546(17) 0.36100(15) 0.0105(4) Uani 1 1 d . . . C12 C 0.4446(2) 0.43601(18) 0.37220(16) 0.0132(4) Uani 1 1 d . . . H7 H 0.384(2) 0.3818(19) 0.4056(17) 0.014(5) Uiso 1 1 d . . . C13 C 0.4076(2) 0.53196(18) 0.33522(16) 0.0153(4) Uani 1 1 d . . . H8 H 0.321(2) 0.5386(17) 0.3451(15) 0.007(5) Uiso 1 1 d . . . C14 C 0.5061(2) 0.61831(19) 0.28508(17) 0.0168(4) Uani 1 1 d . . . H9 H 0.480(2) 0.6852(19) 0.2570(16) 0.013(5) Uiso 1 1 d . . . C15 C 0.6409(2) 0.60710(19) 0.27300(18) 0.0182(5) Uani 1 1 d . . . H10 H 0.710(3) 0.667(2) 0.2365(18) 0.029(6) Uiso 1 1 d . . . C16 C 0.6800(2) 0.51135(18) 0.31095(17) 0.0152(4) Uani 1 1 d . . . H11 H 0.773(3) 0.5034(19) 0.3022(16) 0.018(5) Uiso 1 1 d . . . C17 C 0.2062(2) 0.24827(17) -0.03474(15) 0.0099(4) Uani 1 1 d . . . C18 C 0.3064(2) 0.35612(18) 0.02581(16) 0.0149(4) Uani 1 1 d . . . H12 H 0.390(3) 0.3619(19) 0.0790(18) 0.016(6) Uiso 1 1 d . . . C19 C 0.2819(3) 0.46382(19) 0.00884(17) 0.0182(5) Uani 1 1 d . . . H13 H 0.353(2) 0.540(2) 0.0517(17) 0.018(6) Uiso 1 1 d . . . C20 C 0.1526(3) 0.46207(19) -0.06676(17) 0.0173(5) Uani 1 1 d . . . H14 H 0.136(2) 0.5309(19) -0.0779(16) 0.013(5) Uiso 1 1 d . . . C21 C -0.0850(2) 0.35400(19) -0.21467(17) 0.0155(4) Uani 1 1 d . . . H15 H -0.101(3) 0.425(2) -0.2172(17) 0.023(6) Uiso 1 1 d . . . C22 C -0.1849(2) 0.25311(19) -0.28452(16) 0.0160(4) Uani 1 1 d . . . H16 H -0.274(3) 0.2509(19) -0.3377(17) 0.021(6) Uiso 1 1 d . . . C23 C -0.1531(2) 0.14748(19) -0.28070(16) 0.0142(4) Uani 1 1 d . . . H17 H -0.218(2) 0.0799(19) -0.3334(16) 0.016(5) Uiso 1 1 d . . . C24 C -0.0249(2) 0.14342(17) -0.20500(16) 0.0109(4) Uani 1 1 d . . . C25 C 0.0767(2) 0.24496(17) -0.12407(15) 0.0102(4) Uani 1 1 d . . . C26 C 0.0484(2) 0.35434(18) -0.13503(16) 0.0125(4) Uani 1 1 d . . . C27 C 0.1537(2) 0.05088(16) -0.30046(15) 0.0110(4) Uani 1 1 d . . . C28 C 0.2831(2) 0.02116(17) -0.26667(17) 0.0138(4) Uani 1 1 d . . . H18 H 0.303(2) -0.0101(18) -0.2000(17) 0.013(5) Uiso 1 1 d . . . C29 C 0.3848(2) 0.03685(18) -0.33581(18) 0.0184(5) Uani 1 1 d . . . H19 H 0.471(3) 0.0164(19) -0.3123(17) 0.021(6) Uiso 1 1 d . . . C30 C 0.3586(2) 0.08417(18) -0.43742(18) 0.0183(5) Uani 1 1 d . . . H20 H 0.426(3) 0.091(2) -0.4862(18) 0.026(6) Uiso 1 1 d . . . C31 C 0.2317(2) 0.11765(18) -0.46935(17) 0.0171(4) Uani 1 1 d . . . H21 H 0.210(2) 0.1492(19) -0.5422(18) 0.021(6) Uiso 1 1 d . . . C32 C 0.1291(2) 0.10112(18) -0.40134(16) 0.0149(4) Uani 1 1 d . . . H22 H 0.043(2) 0.1216(18) -0.4187(16) 0.014(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.00722(11) 0.01448(11) 0.00911(11) 0.00232(8) 0.00104(8) 0.00434(8) Se2 0.00811(11) 0.01045(11) 0.01067(12) 0.00098(8) -0.00018(8) 0.00366(8) S1 0.0102(2) 0.0190(3) 0.0090(2) 0.0032(2) 0.00347(19) 0.0072(2) S2 0.0102(2) 0.0116(2) 0.0124(3) -0.0002(2) 0.00264(19) 0.0031(2) C1 0.0094(10) 0.0110(10) 0.0145(10) 0.0059(8) 0.0043(8) 0.0049(8) C2 0.0126(10) 0.0179(11) 0.0117(11) 0.0014(9) 0.0012(8) 0.0053(9) C3 0.0183(11) 0.0188(11) 0.0112(11) 0.0012(9) 0.0062(8) 0.0061(9) C4 0.0129(11) 0.0128(10) 0.0176(11) 0.0027(8) 0.0082(9) 0.0054(8) C5 0.0100(10) 0.0150(10) 0.0193(12) 0.0016(9) 0.0054(9) 0.0061(8) C6 0.0083(10) 0.0201(11) 0.0191(12) 0.0002(9) -0.0010(8) 0.0051(9) C7 0.0129(10) 0.0186(11) 0.0118(11) 0.0004(9) 0.0010(8) 0.0064(9) C8 0.0108(10) 0.0133(10) 0.0120(10) 0.0033(8) 0.0042(8) 0.0062(8) C9 0.0099(10) 0.0071(9) 0.0131(10) 0.0022(8) 0.0031(8) 0.0042(8) C10 0.0115(10) 0.0082(10) 0.0151(11) 0.0025(8) 0.0041(8) 0.0043(8) C11 0.0120(10) 0.0135(10) 0.0047(9) -0.0024(8) -0.0012(7) 0.0054(8) C12 0.0094(10) 0.0168(11) 0.0111(10) 0.0013(9) 0.0034(8) 0.0018(9) C13 0.0120(10) 0.0205(11) 0.0135(11) -0.0049(9) 0.0002(8) 0.0087(9) C14 0.0220(11) 0.0139(11) 0.0135(11) -0.0029(9) -0.0001(9) 0.0086(9) C15 0.0218(12) 0.0130(11) 0.0180(11) 0.0005(9) 0.0080(9) 0.0028(9) C16 0.0127(10) 0.0171(11) 0.0151(11) -0.0030(9) 0.0050(8) 0.0041(9) C17 0.0121(10) 0.0113(10) 0.0087(10) 0.0027(8) 0.0032(8) 0.0066(8) C18 0.0143(11) 0.0163(11) 0.0098(10) 0.0016(8) -0.0031(8) 0.0044(9) C19 0.0242(12) 0.0121(11) 0.0123(11) -0.0014(9) -0.0009(9) 0.0031(9) C20 0.0254(12) 0.0147(11) 0.0154(11) 0.0043(9) 0.0049(9) 0.0118(10) C21 0.0191(11) 0.0195(11) 0.0139(11) 0.0066(9) 0.0058(9) 0.0128(9) C22 0.0130(11) 0.0275(12) 0.0107(10) 0.0062(9) 0.0026(8) 0.0114(9) C23 0.0113(10) 0.0187(11) 0.0100(10) -0.0012(9) 0.0011(8) 0.0039(9) C24 0.0115(10) 0.0134(10) 0.0100(10) 0.0024(8) 0.0045(8) 0.0059(8) C25 0.0098(10) 0.0153(10) 0.0070(9) 0.0026(8) 0.0041(7) 0.0052(8) C26 0.0153(10) 0.0174(11) 0.0082(10) 0.0032(8) 0.0056(8) 0.0082(9) C27 0.0117(10) 0.0077(9) 0.0106(10) -0.0036(8) 0.0025(8) 0.0006(8) C28 0.0170(11) 0.0098(10) 0.0144(11) -0.0001(9) 0.0040(8) 0.0047(8) C29 0.0168(11) 0.0140(11) 0.0267(13) 0.0020(9) 0.0074(9) 0.0074(9) C30 0.0197(11) 0.0138(11) 0.0200(12) -0.0017(9) 0.0104(9) 0.0016(9) C31 0.0221(12) 0.0141(11) 0.0115(11) 0.0004(9) 0.0039(9) 0.0028(9) C32 0.0138(11) 0.0131(10) 0.0148(11) -0.0025(8) -0.0008(8) 0.0045(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 C1 1.966(2) . ? Se1 Se2 2.3561(6) . ? Se1 S1 3.0122(9) . ? Se2 C17 1.9577(19) . ? Se2 S2 2.9495(9) . ? S1 C8 1.7723(19) . ? S1 C11 1.7748(19) . ? S2 C24 1.7804(19) . ? S2 C27 1.7938(19) . ? C1 C2 1.374(3) . ? C1 C9 1.437(3) . ? C2 C3 1.406(3) . ? C2 H1 0.92(2) . ? C3 C4 1.362(3) . ? C3 H2 0.94(2) . ? C4 C10 1.411(3) . ? C4 H3 0.91(2) . ? C5 C6 1.360(3) . ? C5 C10 1.417(3) . ? C5 H4 0.90(2) . ? C6 C7 1.407(3) . ? C6 H5 0.97(2) . ? C7 C8 1.375(3) . ? C7 H6 0.99(2) . ? C8 C9 1.432(3) . ? C9 C10 1.441(3) . ? C11 C16 1.390(3) . ? C11 C12 1.391(3) . ? C12 C13 1.378(3) . ? C12 H7 0.88(2) . ? C13 C14 1.391(3) . ? C13 H8 0.898(19) . ? C14 C15 1.383(3) . ? C14 H9 0.97(2) . ? C15 C16 1.389(3) . ? C15 H10 0.98(2) . ? C16 H11 0.96(2) . ? C17 C18 1.370(3) . ? C17 C25 1.442(3) . ? C18 C19 1.404(3) . ? C18 H12 0.89(2) . ? C19 C20 1.360(3) . ? C19 H13 0.97(2) . ? C20 C26 1.414(3) . ? C20 H14 0.90(2) . ? C21 C22 1.360(3) . ? C21 C26 1.419(3) . ? C21 H15 0.92(2) . ? C22 C23 1.403(3) . ? C22 H16 0.94(2) . ? C23 C24 1.377(3) . ? C23 H17 0.94(2) . ? C24 C25 1.432(3) . ? C25 C26 1.433(3) . ? C27 C28 1.388(3) . ? C27 C32 1.391(3) . ? C28 C29 1.391(3) . ? C28 H18 0.912(19) . ? C29 C30 1.383(3) . ? C29 H19 0.93(2) . ? C30 C31 1.390(3) . ? C30 H20 0.95(2) . ? C31 C32 1.386(3) . ? C31 H21 0.98(2) . ? C32 H22 0.92(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Se1 Se2 102.85(6) . . ? C1 Se1 S1 79.54(6) . . ? Se2 Se1 S1 169.622(13) . . ? C17 Se2 Se1 100.70(6) . . ? C17 Se2 S2 79.86(6) . . ? Se1 Se2 S2 179.225(12) . . ? C8 S1 C11 103.26(9) . . ? C8 S1 Se1 86.44(7) . . ? C11 S1 Se1 83.10(6) . . ? C24 S2 C27 101.39(9) . . ? C24 S2 Se2 86.52(6) . . ? C27 S2 Se2 97.83(7) . . ? C2 C1 C9 119.66(18) . . ? C2 C1 Se1 117.90(15) . . ? C9 C1 Se1 122.17(14) . . ? C1 C2 C3 122.13(19) . . ? C1 C2 H1 121.5(14) . . ? C3 C2 H1 116.4(14) . . ? C4 C3 C2 119.87(19) . . ? C4 C3 H2 120.4(12) . . ? C2 C3 H2 119.7(12) . . ? C3 C4 C10 120.47(19) . . ? C3 C4 H3 123.4(14) . . ? C10 C4 H3 116.1(14) . . ? C6 C5 C10 121.70(19) . . ? C6 C5 H4 122.0(13) . . ? C10 C5 H4 116.3(13) . . ? C5 C6 C7 118.80(19) . . ? C5 C6 H5 121.5(12) . . ? C7 C6 H5 119.6(12) . . ? C8 C7 C6 121.55(19) . . ? C8 C7 H6 118.8(13) . . ? C6 C7 H6 119.6(13) . . ? C7 C8 C9 121.69(18) . . ? C7 C8 S1 115.34(15) . . ? C9 C8 S1 122.98(14) . . ? C8 C9 C1 127.20(17) . . ? C8 C9 C10 115.68(17) . . ? C1 C9 C10 117.11(17) . . ? C4 C10 C5 118.93(18) . . ? C4 C10 C9 120.57(18) . . ? C5 C10 C9 120.48(18) . . ? C16 C11 C12 119.99(18) . . ? C16 C11 S1 123.78(15) . . ? C12 C11 S1 116.22(15) . . ? C13 C12 C11 120.48(19) . . ? C13 C12 H7 120.5(13) . . ? C11 C12 H7 119.0(13) . . ? C12 C13 C14 119.89(19) . . ? C12 C13 H8 119.3(12) . . ? C14 C13 H8 120.8(12) . . ? C15 C14 C13 119.58(19) . . ? C15 C14 H9 120.0(12) . . ? C13 C14 H9 120.4(12) . . ? C14 C15 C16 120.98(19) . . ? C14 C15 H10 119.8(13) . . ? C16 C15 H10 119.2(13) . . ? C15 C16 C11 119.08(19) . . ? C15 C16 H11 120.9(12) . . ? C11 C16 H11 120.0(12) . . ? C18 C17 C25 119.63(17) . . ? C18 C17 Se2 119.42(14) . . ? C25 C17 Se2 120.76(14) . . ? C17 C18 C19 122.03(19) . . ? C17 C18 H12 121.9(14) . . ? C19 C18 H12 116.0(14) . . ? C20 C19 C18 119.80(19) . . ? C20 C19 H13 118.1(12) . . ? C18 C19 H13 122.1(13) . . ? C19 C20 C26 120.58(19) . . ? C19 C20 H14 120.4(13) . . ? C26 C20 H14 118.9(13) . . ? C22 C21 C26 121.71(19) . . ? C22 C21 H15 121.2(14) . . ? C26 C21 H15 117.1(14) . . ? C21 C22 C23 119.36(19) . . ? C21 C22 H16 123.1(13) . . ? C23 C22 H16 117.5(13) . . ? C24 C23 C22 121.03(19) . . ? C24 C23 H17 119.9(12) . . ? C22 C23 H17 119.0(12) . . ? C23 C24 C25 121.28(18) . . ? C23 C24 S2 117.23(15) . . ? C25 C24 S2 121.40(14) . . ? C24 C25 C26 116.55(17) . . ? C24 C25 C17 126.31(17) . . ? C26 C25 C17 117.13(17) . . ? C20 C26 C21 120.06(18) . . ? C20 C26 C25 120.30(18) . . ? C21 C26 C25 119.64(18) . . ? C28 C27 C32 119.91(18) . . ? C28 C27 S2 117.55(14) . . ? C32 C27 S2 122.30(15) . . ? C27 C28 C29 120.10(19) . . ? C27 C28 H18 121.4(12) . . ? C29 C28 H18 118.5(12) . . ? C30 C29 C28 120.0(2) . . ? C30 C29 H19 120.6(13) . . ? C28 C29 H19 119.4(13) . . ? C29 C30 C31 119.83(19) . . ? C29 C30 H20 119.6(13) . . ? C31 C30 H20 120.6(13) . . ? C32 C31 C30 120.41(19) . . ? C32 C31 H21 118.9(12) . . ? C30 C31 H21 120.6(12) . . ? C31 C32 C27 119.67(19) . . ? C31 C32 H22 123.8(12) . . ? C27 C32 H22 116.5(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Se1 Se2 C17 -91.50(8) . . . . ? S1 Se1 Se2 C17 10.74(9) . . . . ? C1 Se1 Se2 S2 44.3(10) . . . . ? S1 Se1 Se2 S2 146.6(10) . . . . ? C1 Se1 S1 C8 -9.79(8) . . . . ? Se2 Se1 S1 C8 -114.12(9) . . . . ? C1 Se1 S1 C11 94.04(8) . . . . ? Se2 Se1 S1 C11 -10.29(10) . . . . ? C17 Se2 S2 C24 -17.57(8) . . . . ? Se1 Se2 S2 C24 -153.5(10) . . . . ? C17 Se2 S2 C27 83.47(8) . . . . ? Se1 Se2 S2 C27 -52.5(10) . . . . ? Se2 Se1 C1 C2 -5.16(16) . . . . ? S1 Se1 C1 C2 -174.84(15) . . . . ? Se2 Se1 C1 C9 -179.10(14) . . . . ? S1 Se1 C1 C9 11.22(14) . . . . ? C9 C1 C2 C3 3.2(3) . . . . ? Se1 C1 C2 C3 -170.92(16) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C2 C3 C4 C10 -2.8(3) . . . . ? C10 C5 C6 C7 -1.0(3) . . . . ? C5 C6 C7 C8 1.8(3) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C6 C7 C8 S1 179.82(16) . . . . ? C11 S1 C8 C7 107.29(16) . . . . ? Se1 S1 C8 C7 -170.67(16) . . . . ? C11 S1 C8 C9 -73.11(17) . . . . ? Se1 S1 C8 C9 8.94(15) . . . . ? C7 C8 C9 C1 176.14(18) . . . . ? S1 C8 C9 C1 -3.4(3) . . . . ? C7 C8 C9 C10 -2.8(3) . . . . ? S1 C8 C9 C10 177.62(14) . . . . ? C2 C1 C9 C8 176.14(17) . . . . ? Se1 C1 C9 C8 -10.0(3) . . . . ? C2 C1 C9 C10 -4.9(3) . . . . ? Se1 C1 C9 C10 168.91(13) . . . . ? C3 C4 C10 C5 179.37(18) . . . . ? C3 C4 C10 C9 0.8(3) . . . . ? C6 C5 C10 C4 179.69(18) . . . . ? C6 C5 C10 C9 -1.8(3) . . . . ? C8 C9 C10 C4 -177.94(17) . . . . ? C1 C9 C10 C4 3.0(3) . . . . ? C8 C9 C10 C5 3.6(3) . . . . ? C1 C9 C10 C5 -175.50(17) . . . . ? C8 S1 C11 C16 -13.99(19) . . . . ? Se1 S1 C11 C16 -98.67(17) . . . . ? C8 S1 C11 C12 166.96(15) . . . . ? Se1 S1 C11 C12 82.29(15) . . . . ? C16 C11 C12 C13 -0.8(3) . . . . ? S1 C11 C12 C13 178.32(15) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C13 C14 C15 C16 -0.5(3) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? C12 C11 C16 C15 0.2(3) . . . . ? S1 C11 C16 C15 -178.85(15) . . . . ? Se1 Se2 C17 C18 13.00(16) . . . . ? S2 Se2 C17 C18 -166.45(16) . . . . ? Se1 Se2 C17 C25 -161.96(13) . . . . ? S2 Se2 C17 C25 18.59(13) . . . . ? C25 C17 C18 C19 4.2(3) . . . . ? Se2 C17 C18 C19 -170.82(16) . . . . ? C17 C18 C19 C20 2.4(3) . . . . ? C18 C19 C20 C26 -5.0(3) . . . . ? C26 C21 C22 C23 -2.2(3) . . . . ? C21 C22 C23 C24 2.0(3) . . . . ? C22 C23 C24 C25 2.8(3) . . . . ? C22 C23 C24 S2 -174.01(15) . . . . ? C27 S2 C24 C23 96.72(16) . . . . ? Se2 S2 C24 C23 -165.98(15) . . . . ? C27 S2 C24 C25 -80.09(17) . . . . ? Se2 S2 C24 C25 17.21(15) . . . . ? C23 C24 C25 C26 -7.1(3) . . . . ? S2 C24 C25 C26 169.54(13) . . . . ? C23 C24 C25 C17 174.37(18) . . . . ? S2 C24 C25 C17 -8.9(3) . . . . ? C18 C17 C25 C24 170.59(19) . . . . ? Se2 C17 C25 C24 -14.5(3) . . . . ? C18 C17 C25 C26 -7.9(3) . . . . ? Se2 C17 C25 C26 167.07(13) . . . . ? C19 C20 C26 C21 -179.2(2) . . . . ? C19 C20 C26 C25 1.0(3) . . . . ? C22 C21 C26 C20 177.68(19) . . . . ? C22 C21 C26 C25 -2.5(3) . . . . ? C24 C25 C26 C20 -173.24(17) . . . . ? C17 C25 C26 C20 5.4(3) . . . . ? C24 C25 C26 C21 6.9(3) . . . . ? C17 C25 C26 C21 -174.47(17) . . . . ? C24 S2 C27 C28 135.46(16) . . . . ? Se2 S2 C27 C28 47.46(16) . . . . ? C24 S2 C27 C32 -50.15(18) . . . . ? Se2 S2 C27 C32 -138.15(16) . . . . ? C32 C27 C28 C29 -2.7(3) . . . . ? S2 C27 C28 C29 171.84(15) . . . . ? C27 C28 C29 C30 1.2(3) . . . . ? C28 C29 C30 C31 1.0(3) . . . . ? C29 C30 C31 C32 -1.6(3) . . . . ? C30 C31 C32 C27 0.1(3) . . . . ? C28 C27 C32 C31 2.0(3) . . . . ? S2 C27 C32 C31 -172.22(15) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.382 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.066 # Attachment 'B805678A_2.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 626067' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2_S2Se2 _chemical_melting_point ? _chemical_formula_moiety 'C32 H22 S2 Se2' _chemical_formula_sum 'C32 H22 S2 Se2' _chemical_formula_weight 628.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall ' -C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.3639(5) _cell_length_b 11.9664(4) _cell_length_c 19.4789(6) _cell_angle_alpha 90.00 _cell_angle_beta 118.9946(12) _cell_angle_gamma 90.00 _cell_volume 5171.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 25.49 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2512 _exptl_absorpt_coefficient_mu 3.042 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5813 _exptl_absorpt_correction_T_max 0.7507 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23050 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.49 _reflns_number_total 4812 _reflns_number_gt 3869 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Yadokari-XG _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0276P)^2^+1.6686P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4812 _refine_ls_number_parameters 413 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0603 _refine_ls_wR_factor_gt 0.0566 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.287321(12) 0.26744(2) -0.127634(15) 0.01944(8) Uani 1 1 d . . . C1 C 0.36295(12) 0.2561(2) -0.12822(15) 0.0186(6) Uani 1 1 d . . . C2 C 0.36109(14) 0.2319(2) -0.19914(17) 0.0240(6) Uani 1 1 d . . . H1 H 0.3236(13) 0.226(2) -0.2433(16) 0.025(8) Uiso 1 1 d . . . C3 C 0.41425(14) 0.2233(2) -0.20217(18) 0.0258(7) Uani 1 1 d . . . H2 H 0.4135(11) 0.208(2) -0.2507(16) 0.022(7) Uiso 1 1 d . . . C4 C 0.46915(14) 0.2374(2) -0.13517(18) 0.0285(7) Uani 1 1 d . . . H3 H 0.5063(13) 0.230(2) -0.1362(16) 0.027(8) Uiso 1 1 d . . . C5 C 0.47099(14) 0.2616(3) -0.06488(19) 0.0327(7) Uani 1 1 d . . . H4 H 0.5061(12) 0.269(2) -0.0208(16) 0.021(8) Uiso 1 1 d . . . C6 C 0.41763(13) 0.2720(2) -0.06137(17) 0.0273(7) Uani 1 1 d . . . H5 H 0.4202(12) 0.289(2) -0.0140(16) 0.026(8) Uiso 1 1 d . . . C7 C 0.31539(11) 0.2320(2) -0.01892(15) 0.0186(6) Uani 1 1 d . . . C8 C 0.31694(12) 0.3215(2) 0.02580(16) 0.0218(6) Uani 1 1 d . . . H6 H 0.3045(11) 0.385(2) 0.0026(15) 0.013(7) Uiso 1 1 d . . . C9 C 0.33504(12) 0.3108(2) 0.10595(16) 0.0235(6) Uani 1 1 d . . . H7 H 0.3328(12) 0.373(2) 0.1334(16) 0.031(8) Uiso 1 1 d . . . C10 C 0.35341(12) 0.2101(2) 0.14050(17) 0.0241(7) Uani 1 1 d . . . H8 H 0.3639(11) 0.202(2) 0.1914(16) 0.020(7) Uiso 1 1 d . . . C11 C 0.35429(11) 0.1147(2) 0.09800(15) 0.0190(6) Uani 1 1 d . . . C12 C 0.37773(12) 0.0129(2) 0.13867(16) 0.0224(6) Uani 1 1 d . . . H9 H 0.3925(11) 0.015(2) 0.1908(15) 0.018(7) Uiso 1 1 d . . . C13 C 0.38076(12) -0.0779(2) 0.10002(16) 0.0236(6) Uani 1 1 d . . . H10 H 0.3967(11) -0.144(2) 0.1248(15) 0.017(7) Uiso 1 1 d . . . C14 C 0.35752(12) -0.0748(2) 0.01827(16) 0.0212(6) Uani 1 1 d . . . H11 H 0.3595(11) -0.140(2) -0.0055(16) 0.025(8) Uiso 1 1 d . . . C15 C 0.33228(11) 0.0205(2) -0.02456(14) 0.0175(6) Uani 1 1 d . . . C16 C 0.33298(11) 0.1228(2) 0.01517(14) 0.0167(6) Uani 1 1 d . . . S1 S 0.29582(3) 0.01379(5) -0.13091(4) 0.01547(14) Uani 1 1 d . . . S2 S 0.30245(3) -0.15277(5) -0.15453(4) 0.01547(14) Uani 1 1 d . . . C17 C 0.37846(11) -0.1662(2) -0.14081(14) 0.0184(6) Uani 1 1 d . . . C18 C 0.41541(12) -0.0738(2) -0.11749(17) 0.0253(7) Uani 1 1 d . . . H12 H 0.4012(12) -0.002(2) -0.1060(15) 0.030(8) Uiso 1 1 d . . . C19 C 0.47272(13) -0.0759(3) -0.11229(18) 0.0284(7) Uani 1 1 d . . . H13 H 0.4957(13) -0.014(3) -0.0936(17) 0.041(9) Uiso 1 1 d . . . C20 C 0.49245(13) -0.1697(3) -0.13168(17) 0.0276(7) Uani 1 1 d . . . H14 H 0.5311(12) -0.174(2) -0.1263(15) 0.028(8) Uiso 1 1 d . . . C21 C 0.45704(12) -0.2681(2) -0.15386(15) 0.0226(6) Uani 1 1 d . . . C22 C 0.47887(13) -0.3640(3) -0.17517(16) 0.0273(7) Uani 1 1 d . . . H15 H 0.5183(12) -0.360(2) -0.1688(16) 0.032(8) Uiso 1 1 d . . . C23 C 0.44597(13) -0.4590(3) -0.19864(17) 0.0288(7) Uani 1 1 d . . . H16 H 0.4591(11) -0.522(2) -0.2141(15) 0.023(7) Uiso 1 1 d . . . C24 C 0.39114(13) -0.4652(3) -0.19761(16) 0.0251(7) Uani 1 1 d . . . H17 H 0.3705(11) -0.530(2) -0.2096(15) 0.019(7) Uiso 1 1 d . . . C25 C 0.36837(11) -0.3754(2) -0.17688(14) 0.0186(6) Uani 1 1 d . . . C26 C 0.39895(11) -0.2700(2) -0.15712(14) 0.0180(6) Uani 1 1 d . . . Se2 Se 0.294437(12) -0.40721(2) -0.175765(15) 0.01994(8) Uani 1 1 d . . . C27 C 0.32303(11) -0.4007(2) -0.06482(15) 0.0177(6) Uani 1 1 d . . . C28 C 0.38230(12) -0.4216(2) -0.00957(16) 0.0223(6) Uani 1 1 d . . . H18 H 0.4104(12) -0.438(2) -0.0244(16) 0.027(8) Uiso 1 1 d . . . C29 C 0.39933(13) -0.4167(2) 0.06948(16) 0.0263(7) Uani 1 1 d . . . H19 H 0.4400(12) -0.430(2) 0.1063(16) 0.024(8) Uiso 1 1 d . . . C30 C 0.35757(14) -0.3935(2) 0.09402(17) 0.0270(7) Uani 1 1 d . . . H20 H 0.3701(13) -0.389(2) 0.1471(19) 0.042(9) Uiso 1 1 d . . . C31 C 0.29817(14) -0.3745(2) 0.03849(17) 0.0250(7) Uani 1 1 d . . . H21 H 0.2692(11) -0.360(2) 0.0515(15) 0.018(7) Uiso 1 1 d . . . C32 C 0.28094(13) -0.3774(2) -0.04068(17) 0.0215(6) Uani 1 1 d . . . H22 H 0.2418(12) -0.364(2) -0.0772(16) 0.029(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.02208(15) 0.01798(15) 0.01977(15) 0.00137(11) 0.01133(12) 0.00050(11) C1 0.0235(15) 0.0138(14) 0.0226(15) 0.0015(11) 0.0145(13) -0.0009(11) C2 0.0281(17) 0.0216(15) 0.0222(16) -0.0009(12) 0.0122(14) -0.0049(13) C3 0.0362(18) 0.0224(16) 0.0287(17) -0.0035(13) 0.0236(15) -0.0035(13) C4 0.0258(17) 0.0292(17) 0.0379(19) 0.0037(14) 0.0212(16) 0.0003(13) C5 0.0202(17) 0.049(2) 0.0255(18) 0.0031(15) 0.0087(15) -0.0052(15) C6 0.0281(17) 0.0361(18) 0.0191(16) 0.0006(13) 0.0125(14) -0.0054(13) C7 0.0191(14) 0.0195(14) 0.0194(14) -0.0032(11) 0.0109(12) -0.0042(11) C8 0.0231(15) 0.0181(15) 0.0268(16) -0.0004(13) 0.0141(13) -0.0031(13) C9 0.0268(16) 0.0228(16) 0.0266(16) -0.0131(13) 0.0174(13) -0.0091(13) C10 0.0240(16) 0.0344(18) 0.0184(16) -0.0080(13) 0.0137(13) -0.0082(13) C11 0.0153(14) 0.0260(15) 0.0171(14) -0.0023(11) 0.0090(12) -0.0044(11) C12 0.0221(15) 0.0302(17) 0.0134(15) 0.0015(13) 0.0074(13) -0.0011(13) C13 0.0234(16) 0.0246(17) 0.0209(15) 0.0070(13) 0.0093(13) 0.0039(13) C14 0.0239(15) 0.0206(16) 0.0202(15) -0.0021(12) 0.0116(13) -0.0001(12) C15 0.0165(14) 0.0220(15) 0.0150(13) 0.0010(11) 0.0084(12) -0.0006(11) C16 0.0135(13) 0.0202(14) 0.0170(14) -0.0011(11) 0.0079(11) -0.0030(11) S1 0.0197(3) 0.0131(3) 0.0132(3) -0.0005(3) 0.0075(3) 0.0007(3) S2 0.0167(3) 0.0133(3) 0.0169(3) -0.0017(3) 0.0086(3) -0.0005(3) C17 0.0176(14) 0.0213(15) 0.0170(14) 0.0022(11) 0.0090(12) 0.0023(11) C18 0.0236(16) 0.0216(16) 0.0308(17) 0.0007(13) 0.0132(14) 0.0000(12) C19 0.0199(16) 0.0282(18) 0.0365(18) 0.0004(14) 0.0131(14) -0.0061(13) C20 0.0196(16) 0.0376(19) 0.0283(16) 0.0077(14) 0.0137(14) 0.0016(14) C21 0.0227(15) 0.0293(16) 0.0175(14) 0.0049(12) 0.0111(13) 0.0037(12) C22 0.0244(17) 0.0375(19) 0.0229(16) 0.0050(13) 0.0137(14) 0.0079(14) C23 0.0319(18) 0.0315(18) 0.0250(16) -0.0021(14) 0.0153(14) 0.0113(14) C24 0.0308(17) 0.0224(16) 0.0199(15) -0.0013(12) 0.0105(13) 0.0012(14) C25 0.0204(14) 0.0221(15) 0.0127(13) -0.0002(11) 0.0076(12) 0.0012(11) C26 0.0201(14) 0.0222(15) 0.0117(13) 0.0029(11) 0.0078(12) 0.0021(11) Se2 0.02157(15) 0.01819(15) 0.01810(14) -0.00065(11) 0.00806(12) -0.00233(11) C27 0.0216(14) 0.0121(13) 0.0193(14) 0.0022(11) 0.0098(12) -0.0017(11) C28 0.0205(15) 0.0232(16) 0.0236(15) 0.0038(12) 0.0111(13) 0.0020(12) C29 0.0243(17) 0.0250(16) 0.0219(16) 0.0040(13) 0.0052(14) -0.0017(13) C30 0.0417(19) 0.0175(15) 0.0212(16) 0.0001(12) 0.0149(15) -0.0056(13) C31 0.0344(18) 0.0184(15) 0.0304(17) -0.0008(12) 0.0220(15) -0.0001(13) C32 0.0195(15) 0.0196(15) 0.0255(16) 0.0028(12) 0.0110(13) 0.0014(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 C7 1.926(3) . ? Se1 C1 1.929(3) . ? Se1 S1 3.0458(7) . ? C1 C6 1.380(4) . ? C1 C2 1.390(4) . ? C2 C3 1.382(4) . ? C2 H1 0.93(3) . ? C3 C4 1.382(4) . ? C3 H2 0.95(3) . ? C4 C5 1.378(4) . ? C4 H3 0.96(3) . ? C5 C6 1.393(4) . ? C5 H4 0.89(3) . ? C6 H5 0.92(3) . ? C7 C8 1.369(4) . ? C7 C16 1.435(3) . ? C8 C9 1.404(4) . ? C8 H6 0.86(3) . ? C9 C10 1.348(4) . ? C9 H7 0.93(3) . ? C10 C11 1.417(4) . ? C10 H8 0.90(3) . ? C11 C12 1.417(4) . ? C11 C16 1.435(3) . ? C12 C13 1.345(4) . ? C12 H9 0.90(2) . ? C13 C14 1.405(4) . ? C13 H10 0.92(3) . ? C14 C15 1.374(4) . ? C14 H11 0.92(3) . ? C15 C16 1.444(4) . ? C15 S1 1.815(2) . ? S1 S2 2.0706(9) . ? S2 C17 1.821(2) . ? S2 Se2 3.0662(7) . ? C17 C18 1.376(4) . ? C17 C26 1.440(4) . ? C18 C19 1.408(4) . ? C18 H12 1.00(3) . ? C19 C20 1.355(4) . ? C19 H13 0.91(3) . ? C20 C21 1.415(4) . ? C20 H14 0.93(3) . ? C21 C22 1.421(4) . ? C21 C26 1.444(4) . ? C22 C23 1.352(4) . ? C22 H15 0.95(3) . ? C23 C24 1.403(4) . ? C23 H16 0.93(3) . ? C24 C25 1.371(4) . ? C24 H17 0.90(3) . ? C25 C26 1.432(4) . ? C25 Se2 1.924(3) . ? Se2 C27 1.919(3) . ? C27 C28 1.383(4) . ? C27 C32 1.388(4) . ? C28 C29 1.384(4) . ? C28 H18 0.91(3) . ? C29 C30 1.385(4) . ? C29 H19 0.94(3) . ? C30 C31 1.383(4) . ? C30 H20 0.92(3) . ? C31 C32 1.384(4) . ? C31 H21 0.90(2) . ? C32 H22 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 Se1 C1 98.76(11) . . ? C7 Se1 S1 79.12(8) . . ? C1 Se1 S1 81.31(7) . . ? C6 C1 C2 120.1(3) . . ? C6 C1 Se1 122.2(2) . . ? C2 C1 Se1 117.8(2) . . ? C3 C2 C1 119.6(3) . . ? C3 C2 H1 122.6(17) . . ? C1 C2 H1 117.7(17) . . ? C2 C3 C4 120.6(3) . . ? C2 C3 H2 120.4(16) . . ? C4 C3 H2 119.1(16) . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H3 118.8(17) . . ? C3 C4 H3 121.4(16) . . ? C4 C5 C6 120.1(3) . . ? C4 C5 H4 120.9(17) . . ? C6 C5 H4 119.0(17) . . ? C1 C6 C5 119.8(3) . . ? C1 C6 H5 121.9(17) . . ? C5 C6 H5 118.3(17) . . ? C8 C7 C16 120.7(2) . . ? C8 C7 Se1 114.1(2) . . ? C16 C7 Se1 125.15(19) . . ? C7 C8 C9 121.9(3) . . ? C7 C8 H6 117.7(17) . . ? C9 C8 H6 120.2(17) . . ? C10 C9 C8 119.0(3) . . ? C10 C9 H7 121.8(17) . . ? C8 C9 H7 119.1(17) . . ? C9 C10 C11 121.9(3) . . ? C9 C10 H8 119.9(17) . . ? C11 C10 H8 118.2(17) . . ? C12 C11 C10 119.2(2) . . ? C12 C11 C16 121.0(2) . . ? C10 C11 C16 119.9(2) . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H9 123.2(17) . . ? C11 C12 H9 116.4(17) . . ? C12 C13 C14 120.4(3) . . ? C12 C13 H10 122.4(16) . . ? C14 C13 H10 117.1(16) . . ? C15 C14 C13 121.8(3) . . ? C15 C14 H11 121.3(17) . . ? C13 C14 H11 116.9(17) . . ? C14 C15 C16 119.8(2) . . ? C14 C15 S1 119.1(2) . . ? C16 C15 S1 121.07(19) . . ? C7 C16 C11 116.5(2) . . ? C7 C16 C15 127.1(2) . . ? C11 C16 C15 116.4(2) . . ? C15 S1 S2 104.17(9) . . ? C15 S1 Se1 86.23(8) . . ? S2 S1 Se1 167.98(3) . . ? C17 S2 S1 104.28(9) . . ? C17 S2 Se2 85.89(8) . . ? S1 S2 Se2 168.12(3) . . ? C18 C17 C26 120.3(2) . . ? C18 C17 S2 118.7(2) . . ? C26 C17 S2 120.90(19) . . ? C17 C18 C19 121.6(3) . . ? C17 C18 H12 120.2(16) . . ? C19 C18 H12 118.2(16) . . ? C20 C19 C18 120.2(3) . . ? C20 C19 H13 122.7(19) . . ? C18 C19 H13 117.1(19) . . ? C19 C20 C21 120.6(3) . . ? C19 C20 H14 121.7(17) . . ? C21 C20 H14 117.5(17) . . ? C20 C21 C22 118.8(3) . . ? C20 C21 C26 120.7(3) . . ? C22 C21 C26 120.5(3) . . ? C23 C22 C21 120.9(3) . . ? C23 C22 H15 121.6(17) . . ? C21 C22 H15 117.3(17) . . ? C22 C23 C24 119.6(3) . . ? C22 C23 H16 122.2(16) . . ? C24 C23 H16 118.2(16) . . ? C25 C24 C23 121.7(3) . . ? C25 C24 H17 118.5(16) . . ? C23 C24 H17 119.8(16) . . ? C24 C25 C26 121.3(2) . . ? C24 C25 Se2 113.6(2) . . ? C26 C25 Se2 125.11(19) . . ? C25 C26 C17 127.8(2) . . ? C25 C26 C21 115.7(2) . . ? C17 C26 C21 116.5(2) . . ? C27 Se2 C25 99.57(10) . . ? C27 Se2 S2 81.02(7) . . ? C25 Se2 S2 78.68(8) . . ? C28 C27 C32 119.8(2) . . ? C28 C27 Se2 123.0(2) . . ? C32 C27 Se2 117.18(19) . . ? C27 C28 C29 119.6(3) . . ? C27 C28 H18 121.0(17) . . ? C29 C28 H18 119.5(17) . . ? C28 C29 C30 120.9(3) . . ? C28 C29 H19 118.4(16) . . ? C30 C29 H19 120.6(16) . . ? C31 C30 C29 119.2(3) . . ? C31 C30 H20 121.3(19) . . ? C29 C30 H20 119.4(19) . . ? C30 C31 C32 120.2(3) . . ? C30 C31 H21 122.6(16) . . ? C32 C31 H21 117.2(16) . . ? C31 C32 C27 120.2(3) . . ? C31 C32 H22 120.0(17) . . ? C27 C32 H22 119.8(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 Se1 C1 C6 -25.6(2) . . . . ? S1 Se1 C1 C6 -103.1(2) . . . . ? C7 Se1 C1 C2 155.0(2) . . . . ? S1 Se1 C1 C2 77.5(2) . . . . ? C6 C1 C2 C3 0.4(4) . . . . ? Se1 C1 C2 C3 179.8(2) . . . . ? C1 C2 C3 C4 0.7(4) . . . . ? C2 C3 C4 C5 -0.8(4) . . . . ? C3 C4 C5 C6 -0.1(5) . . . . ? C2 C1 C6 C5 -1.3(4) . . . . ? Se1 C1 C6 C5 179.3(2) . . . . ? C4 C5 C6 C1 1.2(5) . . . . ? C1 Se1 C7 C8 107.7(2) . . . . ? S1 Se1 C7 C8 -172.9(2) . . . . ? C1 Se1 C7 C16 -73.0(2) . . . . ? S1 Se1 C7 C16 6.3(2) . . . . ? C16 C7 C8 C9 -0.6(4) . . . . ? Se1 C7 C8 C9 178.7(2) . . . . ? C7 C8 C9 C10 2.3(4) . . . . ? C8 C9 C10 C11 -0.7(4) . . . . ? C9 C10 C11 C12 176.0(3) . . . . ? C9 C10 C11 C16 -2.5(4) . . . . ? C10 C11 C12 C13 -177.9(3) . . . . ? C16 C11 C12 C13 0.5(4) . . . . ? C11 C12 C13 C14 -3.7(4) . . . . ? C12 C13 C14 C15 1.4(4) . . . . ? C13 C14 C15 C16 4.3(4) . . . . ? C13 C14 C15 S1 -173.2(2) . . . . ? C8 C7 C16 C11 -2.5(4) . . . . ? Se1 C7 C16 C11 178.25(17) . . . . ? C8 C7 C16 C15 178.3(2) . . . . ? Se1 C7 C16 C15 -0.9(4) . . . . ? C12 C11 C16 C7 -174.4(2) . . . . ? C10 C11 C16 C7 4.0(3) . . . . ? C12 C11 C16 C15 4.9(3) . . . . ? C10 C11 C16 C15 -176.7(2) . . . . ? C14 C15 C16 C7 172.0(2) . . . . ? S1 C15 C16 C7 -10.5(4) . . . . ? C14 C15 C16 C11 -7.2(4) . . . . ? S1 C15 C16 C11 170.34(17) . . . . ? C14 C15 S1 S2 2.2(2) . . . . ? C16 C15 S1 S2 -175.37(18) . . . . ? C14 C15 S1 Se1 -171.7(2) . . . . ? C16 C15 S1 Se1 10.75(19) . . . . ? C7 Se1 S1 C15 -8.30(11) . . . . ? C1 Se1 S1 C15 92.43(11) . . . . ? C7 Se1 S1 S2 -158.55(18) . . . . ? C1 Se1 S1 S2 -57.82(18) . . . . ? C15 S1 S2 C17 -81.34(12) . . . . ? Se1 S1 S2 C17 67.95(19) . . . . ? C15 S1 S2 Se2 67.00(19) . . . . ? Se1 S1 S2 Se2 -143.71(13) . . . . ? S1 S2 C17 C18 1.5(2) . . . . ? Se2 S2 C17 C18 -172.3(2) . . . . ? S1 S2 C17 C26 -175.89(18) . . . . ? Se2 S2 C17 C26 10.32(19) . . . . ? C26 C17 C18 C19 2.9(4) . . . . ? S2 C17 C18 C19 -174.5(2) . . . . ? C17 C18 C19 C20 1.1(4) . . . . ? C18 C19 C20 C21 -2.9(4) . . . . ? C19 C20 C21 C22 178.8(3) . . . . ? C19 C20 C21 C26 0.7(4) . . . . ? C20 C21 C22 C23 -178.3(3) . . . . ? C26 C21 C22 C23 -0.2(4) . . . . ? C21 C22 C23 C24 -3.8(4) . . . . ? C22 C23 C24 C25 3.2(4) . . . . ? C23 C24 C25 C26 1.6(4) . . . . ? C23 C24 C25 Se2 -177.5(2) . . . . ? C24 C25 C26 C17 174.3(3) . . . . ? Se2 C25 C26 C17 -6.8(4) . . . . ? C24 C25 C26 C21 -5.2(4) . . . . ? Se2 C25 C26 C21 173.66(18) . . . . ? C18 C17 C26 C25 175.6(3) . . . . ? S2 C17 C26 C25 -7.0(4) . . . . ? C18 C17 C26 C21 -4.9(4) . . . . ? S2 C17 C26 C21 172.48(18) . . . . ? C20 C21 C26 C25 -177.3(2) . . . . ? C22 C21 C26 C25 4.6(4) . . . . ? C20 C21 C26 C17 3.2(4) . . . . ? C22 C21 C26 C17 -175.0(2) . . . . ? C24 C25 Se2 C27 110.3(2) . . . . ? C26 C25 Se2 C27 -68.7(2) . . . . ? C24 C25 Se2 S2 -170.9(2) . . . . ? C26 C25 Se2 S2 10.1(2) . . . . ? C17 S2 Se2 C27 91.85(11) . . . . ? S1 S2 Se2 C27 -57.49(18) . . . . ? C17 S2 Se2 C25 -9.88(11) . . . . ? S1 S2 Se2 C25 -159.22(18) . . . . ? C25 Se2 C27 C28 -25.9(2) . . . . ? S2 Se2 C27 C28 -102.8(2) . . . . ? C25 Se2 C27 C32 156.1(2) . . . . ? S2 Se2 C27 C32 79.32(19) . . . . ? C32 C27 C28 C29 -1.3(4) . . . . ? Se2 C27 C28 C29 -179.2(2) . . . . ? C27 C28 C29 C30 1.4(4) . . . . ? C28 C29 C30 C31 -0.3(4) . . . . ? C29 C30 C31 C32 -0.8(4) . . . . ? C30 C31 C32 C27 0.8(4) . . . . ? C28 C27 C32 C31 0.2(4) . . . . ? Se2 C27 C32 C31 178.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.384 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.068